Sodium Carbonate → HCID 57937834, compound

HRID 1435076Notes

Reaction equation

HRID 1435076 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17](Br)=[C:16]([CH3:21])[CH:15]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].[N+:23]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)([O-:25])=[O:24].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:29]2[CH:30]=[CH:31][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=2)=[C:16]([CH3:21])[CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27735524-Nitrophenylboronic acidHCID 57937818HCID 57937818, compound

Product 1

HCID 57937834HCID 57937834, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

(4-Bromo-3-methyl-benzyl)-(3-methyl-butyl)-carbamic acid tert-butyl ester (I-2c: 250 mg, 0.675 mmol) was added to a 5 mL microwave vial and dissolved in 2 mL of 1,2-dimethoxyethane. To this solution was added 4-nitro-phenyl boronic acid (146 mg, 0.878 mmol) and 1 mL of a 2M aqueous sodium carbonate solution and tetrakis(triphenylphosphine) palladium (0.040 g, 0.0338 mmol). The reaction mixture was purged with nitrogen and sealed before heating to 80° C. by microwave irradiation for 15 minutes. The reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified using preparative thin layer chromatography eluting with 15% ethyl acetate in heptane. Collection and extraction of the product-containing band followed by concentration under reduced pressure afforded the title compound (I-8a: 0.150 g).

Workup

  1. customThe reaction mixture was purged with nitrogen
  2. customsealed
  3. additionThe reaction mixture was diluted with water (10 mL)
  4. extractionextracted with ethyl acetate (2×10 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified
  10. washeluting with 15% ethyl acetate in heptane
  11. customCollection and extraction of the product-containing band
  12. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-e46f059a50ca44999a3a5925731b9323
Source dataset
uspto-grants-2009_11
Patent number
US07615651B2

Reaction notes

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